76106-76-8

Usage

InChI:InChI=1/C16H16O2/c1-18-15-9-5-8-14(12-15)16(17)11-10-13-6-3-2-4-7-13/h2-9,12H,10-11H2,1H3

Upstream product

• 22966-24-1 1-(3-methoxyphenyl)-3-phenyl-2-propene-1-one 
• 104-53-0 3-phenyl-propionaldehyde 
• 2845-89-8 1-chloro-3-methoxy-benzene 
• 100-42-5 styrene 
• 1273592-78-1 (3-methoxy-benzylidene)-(3-methyl-pyridin-2-yl)-amine 
• 501-52-0 3-Phenylpropionic acid 
• 192569-03-2 sodium tetrakis(3-methoxyphenyl)borate 
• 100-51-6 benzyl alcohol 
• 586-37-8 1-(3-Methoxyphenyl)ethanone 
• 591-31-1 3-methoxy-benzaldehyde 
• 591-50-4 iodobenzene 
• 58824-50-3 1-(3-methoxyphenyl)-2-propen-1-ol 
• 14371-10-9 (E)-3-phenylpropenal 
• 10365-98-7 3-methoxyphenylboronic acid 

Downstream Products

• 57803-92-6 3-(3-methoxyphenyl)indene 
• 1136238-68-0 C₁₆H₁₆O 

Relevant academic research and scientific papers

Direct conversion of secondary propargyl alcohols into 1,3-di-arylpropanoneviaDBU promoted redox isomerization and palladium assisted chemoselective hydrogenation in a single pot operation

Palladium(ii)acetate is found to be an efficient catalyst for the single-step conversion of secondary propargyl alcohols to 1,3-diarylpropanone derivatives under mild basic conditions. The reaction is believed to proceedviaredox isomerisation of secondary propargyl alcohols followed by chemoselective reduction of an enone double bond with formic acid as an adequate hydrogen donor. A large number of 1,3-diarylpropanone derivatives may readily be prepared from a milligram to a multigram scale.

BTP-Rh@g-C3N4 as an efficient recyclable catalyst for dehydrogenation and borrowing hydrogen reactions

Highly active catalysts play an important role in modern catalysis. A novel and efficient ligand benzotriazole-pyrimidine (BTP) and the corresponding rhodium composite on C3N4 were successfully synthesized. The resulting rhodium composite was fully characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), x-ray diffraction (XRD), thermogravimetric analysis (TGA), and x-ray photoelectron spectroscopy (XPS). The obtained composite exhibited good catalytic activity and good recovery performance in the synthesis of quinoxaline from 2-aminobenzyl alcohol and benzonitrile, and more than 20 quinoxalines were obtained in good yields. Additionally, it also showed that rhodium composite could achieved good catalytic performance in the synthesis of functionalized ketone through borrowing hydrogen strategy.

Selective catalytic synthesis of α-alkylated ketones and β-disubstituted ketones via acceptorless dehydrogenative cross-coupling of alcohols

Herein, a phosphine-free pincer ruthenium(III) catalyzed β-alkylation of secondary alcohols with primary alcohols to α-alkylated ketones and two different secondary alcohols to β-branched ketones are reported. Notably, this transformation is environmentally benign and atom efficient with H2O and H2 gas as the only byproducts. The protocol is extended to gram-scale reaction and for functionalization of complex vitamin E and cholesterol derivatives.

Ligand-tuned cobalt-containing coordination polymers and applications in water

Ligands play a key role in modern catalysis research and occasionally determine whether a reaction will take place under specific conditions, such as in water. In this experiment, ligands containing an indole-based diacid moiety were employed to prepare the corresponding cobalt coordination polymer material (Co-CIA) and porous oval polymer material (Co-NCIA). Interestingly, it was observed that Co-CIA could promote the alkylation of ketones with alcohols and alcohols with alcohols, while Co-NCIA was effective for the synthesis of 1-benzyl-2-aryl-1H-benzo[d]imidazoles from various phenylenediamine and benzyl alcohols through borrowing hydrogen and dehydrogenation strategies. Other mechanism explorations, such as deuterium labeling experiments and a kinetics study, were conducted to better understand Co-CIA and Co-NCIA systems and the related transformations. Our studies provided an efficient method for the development of highly active cobalt coordination polymer materials with excellent recovery performance for dehydrogenation and borrowing hydrogen reactions under water and base-free conditions.

Iodine-catalyzed α,β-dehydrogenation of ketones and aldehydes generating conjugated enones and enals

A transition metal-free α,β-dehydrogenation of ketones and aldehydes was developed. This reaction was conducted in a facile I2/KI/DMSO system to produce the corresponding unsaturated compounds in good to high yields. The gram-scale experiment also indicated the potential synthetic value of this new reaction in organic synthesis. In the reaction, DMSO acted as both solvent and mild oxidant.

Preparation method of novel aromatic ketone compound

The invention discloses a preparation method of a novel aromatic ketone compound. According to the preparation method, an aromatic carboxylic acid compound and an aromatic olefin compound are used asreaction raw materials, triphenylphosphine is taken as a deoxidizing reagent, Methylenene blue is taken as a photocatalyst, stirring and reacting are carried out at room temperature in an N,N-dimethylacetamide solvent under the irradiation of a white light lamp in a nitrogen atmosphere and under the condition of taking 2,4,6-trimethylpyridine as an alkali, thereby obtaining a target product, namely the aromatic ketone compound. The method has the advantages of mild reaction conditions, simplicity in operation, low cost, convenience in purification, environmental friendliness and the like.

Sustainable and Selective Alkylation of Deactivated Secondary Alcohols to Ketones by Non-bifunctional Pincer N-heterocyclic Carbene Manganese

A sustainable and green route to access diverse functionalized ketones via dehydrogenative–dehydrative cross-coupling of primary and secondary alcohols is demonstrated. This borrowing hydrogen approach employing a pincer N-heterocyclic carbene Mn complex displays high activity and selectivity. A variety of primary and secondary alcohols are well tolerant and result in satisfactory isolated yields. Mechanistic studies suggest that this reaction proceeds via a direct outer-sphere mechanism and the dehydrogenation of the secondary alcohol substrates plays a vital role in the rate-limiting step.

Chemoselective Hydrosilylation of the α,β-Site Double Bond in α,β- And α,β,γ,δ-Unsaturated Ketones Catalyzed by Macrosteric Borane Promoted by Hexafluoro-2-propanol

The B(C6F5)3-catalyzed chemoselective hydrosilylation of α,β- and α,β,γ,δ-unsaturated ketones into the corresponding non-symmetric ketones in mild reaction conditions is developed. Nearly 55 substrates including those bearing reducible functional groups such as alkynyl, alkenyl, cyano, and aromatic heterocycles are chemoselectively hydrosilylated in good to excellent yields. Isotope-labeling studies revealed that hexafluoro-2-propanol also served as a hydrogen source in the process.

Controlling the selectivity and efficiency of the hydrogen borrowing reaction by switching between rhodium and iridium catalysts

The catalytic alkylation of ketones with alcohols via the hydrogen borrowing methodology (HB) has the potential to be a highly efficient approach for forming new carbon-carbon bonds. However, this transformation can result in more than one product being formed. The work reported here utilises bidentate triazole-carbene ligated iridium and rhodium complexes as catalysts for the selective formation of alkylated ketone or alcohol products. Switching from an iridium centre to a rhodium centre in the complex resulted in significant changes in product selectivity. Other factors-base, base loading, solvent and reaction temperature-were also investigated to tune the selectivity further. The optimised conditions were used to demonstrate the scope of the reaction across 17 ketones and 14 alcohols containing a variety of functional groups. A series of mechanistic investigations were performed to probe the reasons behind the product selectivity, including kinetic and deuterium studies.

Nickel-Catalyzed Alkylation of Ketone Enolates: Synthesis of Monoselective Linear Ketones

Herein we have developed a Ni-catalyzed protocol for the synthesis of linear ketones. Aryl, alkyl, and heteroaryl ketones as well as alcohols yielded the monoselective ketones in up to 90% yield. The catalytic protocol was successfully applied in to a gram-scale synthesis. For a practical utility, applications of a steroid derivative, oleyl alcohol, and naproxen alcohol were employed. Preliminary catalytic investigations involving the isolation of a Ni intermediate and defined Ni-H species as well as a series of deuterium-labeling experiments were performed.